White Mountains CEO updates holdings after 1,250 restricted shares vest

White Mountains Insurance Group Chief Executive Officer Wesley C. Bell reported changes in his shareholdings in the company.

Rhea-AI Filing Summary

White Mountains Insurance Group Chief Executive Officer Wesley C. Bell reported changes in his shareholdings in the company. On January 1, 2026, 1,250 restricted common shares became unrestricted, and 425 common shares were withheld by the company to cover his tax obligations at a reported price of $2,078.03. After this transaction, he directly held 1,655 restricted common shares and 2,150 common shares, and indirectly held 8 common shares through the WTM Retirement Plan. The filing is made by a single reporting person in his capacity as Chief Executive Officer.

Insider Trade Summary

Exercise Price or Tax Liability: 425 shares

Exercise Price or Tax Liability 3 txns

Insider Caffrey Liam P

Role Chief Executive Officer

Type	Security	Shares	Price	Value
Exercise Price or Tax Liability	Common Shares	425	$2,078.03	$883K
holding	Common Shares (Restricted)	--	--	--
holding	Common Shares	--	--	--

Holdings After Transaction: Common Shares — 1,655 shares (Direct); Common Shares (Restricted) — 2,150 shares (Direct); Common Shares — 8 shares (Indirect, by WTM Retirement Plan)

Footnotes (2)

1. F1. On January 1, 2026, 1,250 restricted Common Shares became unrestricted. 425 of the Common Shares were withheld by the Company to satisfy the Reporting Person's tax obligations.
2. F2. Reflects accumulation of 2 Common Shares in Reporting Person's Company 401(k) account since his last filed report. The information in this report is based on a plan report dated as of December 22, 2024.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What insider transaction did WTM's CEO report in this filing?

White Mountains Insurance Group Chief Executive Officer Wesley C. Bell reported that on January 1, 2026, 1,250 restricted common shares became unrestricted, with 425 common shares withheld by the company to satisfy his tax obligations.

How many White Mountains Insurance Group (WTM) shares does the CEO now hold?

Following the reported transaction, Wesley C. Bell directly holds 1,655 restricted common shares and 2,150 common shares, and indirectly holds 8 common shares through the WTM Retirement Plan.

What price was reported for the WTM shares withheld for taxes?

The filing shows that the 425 common shares withheld to cover tax obligations were reported at a price of $2,078.03.

What triggered the change in the CEO’s White Mountains restricted shares?

The change was triggered when 1,250 restricted common shares became unrestricted on January 1, 2026, as described in the explanation of responses.

How did the CEO’s retirement or 401(k)-type holdings in WTM change?

The filing notes an accumulation of 2 common shares in Wesley C. Bell’s company 401(k) account since his last report, based on a plan report dated December 22, 2024, bringing his indirect holdings to 8 common shares.

What is Wesley C. Bell’s role and relationship to White Mountains Insurance Group (WTM)?

Wesley C. Bell is identified as an officer of White Mountains Insurance Group Ltd, serving as its Chief Executive Officer, and the filing is made by one reporting person.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Accepted by SEC EDGAR 01/02/2026 - 06:02 PM Learn about SEC filing dates

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Caffrey Liam P

(Last) (First) (Middle)

C/O WHITE MOUNTAINS INSURANCE GROUP, LTD

23 SOUTH MAIN STREET, SUITE 3B

(Street)

HANOVER NH 03755

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
WHITE MOUNTAINS INSURANCE GROUP LTD [ WTM ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	Chief Executive Officer

3. Date of Earliest Transaction (Month/Day/Year)
01/01/2026

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Common Shares	01/01/2026		F		425	D	$2,078.03	1,655(1)	D
Common Shares (Restricted)								2,150(1)	D
Common Shares								8(2)	I	by WTM Retirement Plan

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares

Explanation of Responses:

1. On January 1, 2026, 1,250 restricted Common Shares became unrestricted. 425 of the Common Shares were withheld by the Company to satisfy the Reporting Person's tax obligations.

2. Reflects accumulation of 2 Common Shares in Reporting Person's Company 401(k) account since his last filed report. The information in this report is based on a plan report dated as of December 22, 2024.

	Wesley C. Bell, by Power of Attorney	01/02/2026
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.